What Is the Difference Between a Manhattan, Brooklyn, and Old Fashioned?

My taste for cocktails often follows the seasons and the venue. Summer lunches on a patio equal a vodka lemonade, a football game necessitates a beer, and a nice steak dinner calls for a glass of Cabernet. And inevitably, as the weather gets cooler and the fanciful holiday party season heats up, my taste buds sing for a mixed drink, preferably with a dark liquor, and almost always served in a martini glass.

I know, I know: The glass is for the caché. A drink doesn’t need to be served in an upside down tent where the faintest knock sends liquid splashing around everywhere. But when you have falling snow, delicious hors d’oeuvres, and an excuse to wear that awesome cocktail dress, how can you not have just the right cocktail to go with it?

Or maybe it’s a Wednesday after a hard day of work and you just need a drink.

Whatever your reason, cocktail menus all over are brimming with both classic cocktails from yesteryear and today’s newest mixologist inventions. The Manhattan, the Brooklyn, and the Old Fashioned are just some of those old-timey cocktails that have jumped from the specialty bar menu into the mainstream. While once considered relics of your grandparents’ dinner theater and supper club, the cocktail renaissance of the 21st century has brought all three of these back in vogue. Do you truly know, though, if you’re ordering one and not the other? It’s a more common dilemma than you would think. Whenever somebody orders one of these particular drinks, I always hear a variant of the question, “What’s the difference between those again? I can never remember. Is that the one that’s made with sweet or dry vermouth…?”

So if you’re in the mood for a whiskey cocktail but aren’t sure what to order, or can’t remember which has a cherry versus which has the lemon peel and sugar, pull up your barstool for a bit of history and the small but important differences between these classics.

The Manhattan

The Manhattan is one of the oldest great American cocktails, and one of the first cocktails that used vermouth as a significant part of the recipe, spawning variations too numerous to count (martini, anyone?). It’s widely agreed to have been invented way back in the early 1870s: The most popular story goes that it was created for a political event held at The Manhattan Club in—where else—Manhattan, attended by Jennie Jerome, the mother of Sir Winston Churchill. However, though the Manhattan Club takes credit for inventing the drink, the second part of the story has been roundly debunked as she was supposedly back in Europe quite pregnant with Winston at the time. While it is possible that The Manhattan Club has first honors, another recorded story from around the same time suggests a New York bartender named Black created the first Manhattan in another bar in a different part of town. In the end, we may never know.

Simply put, a classic Manhattan is made with a 2:1 ratio of whiskey and sweet vermouth, a splash of bitters, and almost always garnished with a maraschino cherry. While there are many options for the type of whiskey such as rye, bourbon, or Canadian whiskey, rye is the most common choice. Of course, you don’t have to follow the recipe exactly: Some use dry vermouth, others orange bitters, and you get to argue whether it should be shaken or stirred.

The Brooklyn

The Brooklyn cocktail, much like its eponymous borough, is the Manhattan’s less well-known and often misunderstood cousin. With whiskey, vermouth, and bitters, it’s very similar to the more popular Manhattan. The type of vermouth is one of the main differentiators here: Unlike a Manhattan’s sweet vermouth, classic Brooklyns call for dry. The first written recipe dates back to 1908’s Jack’s Manual, a guide for bartenders and innkeepers, and isn’t often found on bar menus. The main reason is because the remaining ingredients from this recipe are very difficult to procure: Beyond bourbon and vermouth, the original version calls for maraschino liqueur and Amer Picon, a bitter orange aperitif that is virtually impossible to find in the US. However, many of its more modern spinoffs such as the Red Hook cocktail are quite well known.

Should you want to experiment with creating your own classic Brooklyn, substituting the Amer Picon with an Italian amari and, if needed, a dash of orange bitters should do the trick. Again, in theory any whiskey would work well here but go for a strong one such as rye since it needs to hold up to the 1:1 vermouth proportion called for in the original version.

The Old Fashioned

At first glance it may not make sense to include Don Draper’s favorite drink with the other two: Line the three up on a bar and it’s pretty easy to differentiate an Old Fashioned since it’s the only one always served on the rocks. However, it would be remiss to not include what is considered by many to be the first ever cocktail, especially when so many ingredients remain the same. The original definition of the word “cocktail”, invented in the early 19th century, meant any type of liquor mixed with bitters, sugar, and water, and the Old Fashioned as we now know it is pretty much that in a nutshell. The first Old Fashioned formula was originally named the Whiskey Cocktail but eventually morphed into the Old Fashioned: purists, tired of the growing trend of fanciful, experimental cocktail creations throughout the late 19th century, began to demand the original “old fashioned” type of cocktail. A lump of sugar dampened with bitters, muddled with a small spoon, then topped with ice and your choice of rye or bourbon, it’s as close to that original definition of “cocktail” as you can get. And so the modern Old Fashioned was (re-)born.

But with whiskey and bitters as key parts of an Old Fashioned, it’s easy to see how one could occasionally confuse the drink with Manhattans and Brooklyns. Over the years, like any cocktail, it’s gone through many iterations—the addition of muddled fruit being one of the most common—but the classic stands on its own with only a lemon or orange peel as the garnish.

However you like your whiskey, your cocktail glasses, or your garnish, try one of these classic versions or variations and enjoy at the company holiday party or on a cold night in front of the fireplace.

This is the super classic, pure Manhattan cocktail made with a 2:1 proportion of rye and sweet vermouth, a dash of Angostura bitters, and a maraschino cherry for garnish. To really take it a step above, don’t use the neon red super sweet maraschino cherries from your local supermarket. Instead, splurge on the decadent Luxardo brand, the original maraschino cherry. Get our Classic Manhattan recipe.

What makes a Perfect Manhattan perfect is not how it’s mixed, but the type of vermouth used. Not a fan of sweet, but is dry a little too dry? The Perfect Manhattan uses a half and half mix of sweet and dry vermouth. The rest of the classic recipe remains the same. A lemon peel is also an acceptable garnish if a cherry just doesn’t do it for you. Get our Perfect Manhattan recipe.

A variation on the Manhattan, the Rob Roy was created after an operetta of the same name playing in New York at the time. A traditional Rob Roy maintains the same ingredients as a Manhattan but uses Scotch whisky in place of American whiskey. The proportions can be slightly different, too. Perfect or Dry Rob Roys just change the type of vermouth in the same way as a Manhattan would. Get our Rob Roy recipe.

While the originalJack’s Manual Brooklyn calls for a 1:1 ratio of rye and vermouth, most people nowadays will do a Manhattan-like 2:1 ratio. Remember to use maraschino liqueur, which is not the same thing as the juice from a supermarket-brand maraschino cherry jar. Also, unless you are reading this in France there’s no chance you’re going to find Amer Picon in the United States. Go for a orange-flavored Italian Amaro such as CioCiaro, or if you can’t find it, use a regular bitter amaro and just supplement with Angostura orange bitters for that orange flavor. Get our Classic Brooklyn recipe.

Too tired to chase down an Amer Picon substitute? Make a Red Hook, one of the many modern variations on the Brooklyn. The name gives it some authenticity as it’s named after the Red Hook neighborhood of Brooklyn. Heavier on the rye, the sweetness of the vermouth and maraschino liqueur balances it out. Get the recipe.

There are so many versions of Old Fashioneds out there: Some muddle a ton of fruit, others use a splash of soda like Sprite in place of water (or no water at all), and still others use flavored syrups in place of sugar. But the classic is a classic for a reason. You can substitute the sugar cube with simple syrup, but if you do use cubes don’t forget the tiny cocktail spoon for muddling. An orange or lemon peel makes the perfect garnish. Get the recipe.